


Falling for a Boy

by actualcas (PieFeathers), PieFeathers



Category: Supernatural
Genre: Alternate Universe - Human, Bi-Curious Dean Winchester, Depression, Eventual Romance, Eventual Smut, FTM Castiel, First Kiss, First Meetings, Gender Dysphoria, Happy Ending, Homophobia, Human Castiel, M/M, Past Relationship(s), Polyamory, Slice of Life, Suicidal Thoughts, Trans Castiel, Trans Male Character, Transphobia, birthday gift for me
Language: English
Status: In-Progress
Published: 2017-08-11
Updated: 2017-09-17
Packaged: 2018-12-13 22:10:00
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,175
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11769393
Author URL: https://archiveofourown.org/users/PieFeathers/pseuds/actualcas, https://archiveofourown.org/users/PieFeathers/pseuds/PieFeathers
Summary: Castiel is no stranger to having his heart broken. He is often left in the dust by guys due to him being trans. He lives his life day to day and expects to never meet anyone that will want him. On his 24th birthday he meets Dean, a man who he becomes quick friends with. He becomes a steady fixture in Castiel's life and Castiel wonders if this man is the one. The journey to a happy life is filled with angst, heartbreak, anger, love and acceptance of himself.





	1. Chapter 1

**Author's Note:**

> Hey guys so as a birthday present to myself I started this story. It’s a very personal to me so please be kind. I’m writing this because at this current time in my life I’m not really loving myself, I feel alone and just overall in a bad place. I wanted to write a story where someone else is in the same place but it gets better for them. Kind of a personal message of hope to myself and others. Please read the tags for warnings and this is a WIP! Enjoy!

**8/20 8:45 PM**

_Mirrors don’t lie._ Castiel stared at the mirror in despair. He ran a hand along his face, a good amount of facial hair was present, dark against his fair skin, however it wasn’t a beard or stubble as he waited so patiently for. Two years, he sighed. It wasn’t that he wasn’t happy with how he looked, he was just waiting for the day that he felt he looked how he saw himself since he was younger. 

He pulled at his binder, sighing in defeat. He still had about a year until his top surgery and the wait was pure anguish. It was a mix of excitement, nervousness and impatience. 

He was torn back into the present as he felt his fingernails dig into his skin, an unconscious reaction to how he felt about himself. He relaxed his fingers, smoothing over the small crescents on his skin with his palm. 

He took a deep breath and looked himself over in the mirror once more after he pulled on his shirt.  It was more tight fitting than his other shirts. He was very nervous to wear it as sometimes his binder lines would show through.  Castiel wanted to look nice however as his friends all were taking him out to a bar for his birthday. 

Castiel wasn’t too excited for it however. Sure he did love to go out drinking but most of the time he only enjoyed himself when he actually was feeling good about himself. Today was not one of those days. It seemed that those days of self loathing were growing numerous and he couldn’t tell if it was because it was because of his growing loneliness. How sad was his life that he was depressed on his own birthday? 

Castiel shook his head. If his friends wanted to go out to celebrate who was he to say no? He didn’t want to disappoint them and besides he could possibly get drunk enough to not care eventually.  He grabbed his keys and jacket and headed ou t. 

As he walked to his bus stop he though about the past twenty-four years of his life. What had he accomplished in that time? He was single, never having been in a healthy relationship and never as a guy. He worked full time in a job he hated and he had dreams that he never would achieve. He had plenty of friends but sometimes he wondered if they just didn’t tolerate him.  His own dreams and goals seemed to elude him as well. 

His family supported his dreams to be an author like his father. They even supported the weird interests he had growing up like horror stories and taxidermy. He wished they just supported him when he sat down across from his mother and told her he was a boy, and always felt like one.  It took him forever to find the right words to tell her and in a matter of seconds all the confidence he had built up was destroyed by her words, or lack of. 

She ignored him. She acknowledged how he felt but didn’t speak about it with him for another six months.  The silence hurt more than any actual rude words. Of course the refusal of his pronouns and his chosen name stung but eventually he blocked it out and accepted his parent’s just would never care. His father seemed to care more than his mother at least after a while. 

In the beginning his parents acted as if Castiel hadn’t come out as trans at all. When Castiel started hormones they acted like they couldn’t tell that there was a change, even after his voice dropped and his face changed. It was to the point where they refused to believe anyone saw him as a guy, even though the rest of society did.  When he changed his name was when his father, Chuck, finally came around and decided that this might actually be a thing that was really happening. His mother, Naomi, however refused. She was just stuck in her old ways of seeing him as her daughter not her son. 

When he came out as gay however that pissed off Naomi. She told Castiel that he either had to be a straight boy and date women, or he should of just stayed a girl if all he was going to do was date men. She told him it defeated the purpose of him wanting to be a boy. She of course didn’t believe that he could be gay and transgender.  That was when he decided he had enough of trying to talk to Naomi if she wasn’t going to support him through his tough times. 

Her complete lack of understanding did hurt him however.  He began to close in on himself and he started to believe that maybe she was right, a guy wouldn’t be interested in him as a guy. He often thought about that and it caused him a lot of issues. He never told her that it did because he knew what her answer would be. 

Not only did she have a misguided understanding of how transgender and being gay worked but she also had a toxic view of how masculinity should have been. Men weren’t allowed to cry, men weren’t allowed to wear makeup or dance. Men were men, and not allowed to be anything he was. 

Castiel thought he was attractive as a guy, in fact many of his friends were quick to inform of him so. His bright blue eyes mixed with his messy dark brown hair were quiet a show stopper. He wasn’t short but he wasn’t tall by any means either. He was average build with muscle slowly building over time he was working out.  His face was slightly rounder but his jaw was still strong and over all he was a boyish type of handsome. 

The issue was finding guys that simply didn’t care that he was trans. The thing was it all went well until he disclosed this tiny fact. The sad thing was how they treated Castiel like he was a real guy until they found out he was born female. He couldn’t understand. He looked, sounded and acted like a cis guy. He passed very well and if they were to just date romantically guys would just see him as a guy. All it mattered to the guys he liked were if he had a penis or not. 

Castiel grinned at his friends as he entered the bar. Three of them were standing by the bar, drinks already in two of their hands. 

Charlie was an old friend turned roommate. She was there with her girlfriend Jo who Castiel had slowly gotten to know over the short time she had dated Charlie.  Standing next to them was another old friend of his, Benny. Benny was a big dude that would roughen anyone up that said shit to Castiel. 

“ Hey there he is!” Charlie exclaimed as she saw him. 

“Hey Charlie. Jo. Benny.” Castiel nodded to each one in turn. 

“What do you want?” Charlie asked, waving down the bartender.

“Isn’t it a little early for you to be drinking?” Benny spoke up but Castiel just rolled his eyes. 

“It’s his birthday! He can do whatever he wants! If he want’s to get smashed let him!” Charlie hit Benny playfully. 

“ Yeah I really need a drink right now.” Castiel sighed. 

“You alright?” Jo nudged him and he nodded. 

“I’m fine.” He lied. 

Jo didn’t say anything more but knew he was lying. She just didn’t want to push it and ruin the night. Castiel grabbed his drink and they slowly made their way upstairs. 

The bar was a well known gay bar in the community. It boasted three stories, each a different type of area. The lower floor was where the main bar was and were a few tables were for more private groups. The second story was covered in large couches and tables for people to relax and drink. This was Castiel’s favorite area. The third and final story was where the dance floor was at. It was used for clubbing and depending on his mood Castiel spent some time up there but usually never danced with anyone. 

They settled down on a couch, looking around the already crowded bar. Castiel sat back and sipped on his drink, watching the people. It was one of his favorite past times, especially at bars. He kind of zoned out Charlie and Jo talking in the background, and he saw Benny on his phone out of the corner of his eye. 

After about 20 minutes Castiel was growing bored. His attention was drawn to a few good looking guys but most of them were with someone else or ignoring him. He pulled out his phone to play some games but stopped when a group walked by. 

A group of about five guys had just appeared with their drinks and were looking around for a place to sit. One guy in the middle caught Castiel’s attention. He was a little over 6 feet with short brown hair and a freckle splattered face. He was tanned and very handsome, his flannel shirt folded just above his muscular lower arms. He turned to Castiel’s direction and his eyes met with the green ones of the stranger. 

Castiel turned bright red as the man smiled at him and he just froze until the man looked away. He scolded himself for just freezing, what the hell was that? How was he going to be able to find a date if he just kept acting all awkward whenever a hot guy looked his way?

Much to Castiel’s delight the group sat on the couch across the room. He tried his best to subtly look over at the man who was kicked back with a beer in his hand. Castiel felt a jab to his ribs and he turned to see his friends staring at him with the same look on each of their faces. 

“Oh? You staring at the hot boy over there?” Charlie teased. Castiel shook his head and looked down at his drink. 

“No...” He mumbled. Charlie giggled and stood up crossing the room to the group of the friends. 

Castiel’s heart sank as he knew what she was doing. Sure he thought the guy was cute but no way was he going to come over there and talk to him. He also wasn’t sure if the guy would be only interested in hooking up, which Castiel was not into. He shook his head as Charlie looked back at him and gave him the thumbs up as she started to talk to the man. 

As the guy stood up to come over, Castiel felt that he could just die right then. He was not ready to speak to this guy only to get let down once more. 


	2. Chapter 2

**Notes for the Chapter:**

> Sorry about the wait there guys, it's been too long. I need to keep track of how long it is between my posts.

Castiel looked around desperately for some way to escape. He felt like just melting into the floor. He couldn’t believe his friends would do this. He tried to pretend he wasn’t just sitting there waiting for the handsome man to talk to him and instead started to mess around on his phone.

“Hey.” A deep voice alerted Castiel to the presence of the stranger.

A thousand thought’s ran through his head as he worked up the courage to even just look up. What seemed like a few minutes turned out to be a single short second before he finally spoke up.

“H-hey.” His voice cracked as he got a good look at the man.

Up close he was even more attractive and Castiel felt his courage wavering. He scolded himself for his voice cracking like that. It seemed it always did that at the worst times, especially around attractive guys or when Castiel was trying his hardest to appear more masculine.

Why on earth would someone as attractive as this even come over to talk to Castiel? He knew he was not that good looking enough to talk to a guy in that league.

“Dean.” The stranger said.

It took a good minute for Castiel to realize Dean was introducing himself.

“Sorry. Castiel or Cas. Some of my friends call me that.”

“Aw, we’re already friends?” Dean chuckled.

Castiel stammered to answer, trying to defend himself. He wasn’t quiet sure if Dean meant that or not, and Castiel didn’t want to go off his body language. Castiel was never good at deciphering others cues and it often got him into trouble. Social skills was not his thing to say the least.

“I’m teasing you Cas.” Dean winked.

“Oh sorry.” Cas quickly apologized.

“Why?” Dean asked clearly confused. “You don’t have anything to be sorry about.”

Dean sat down across from Castiel and set his drink down onto the table. His confusion slowly turned to worry as he stared at Cas.

“It’s just something I tend to say.” Castiel said.

“Oh okay.” Dean frowned.

_Real smooth,_ Castiel thought,  _He’s going to think I’m a nutcase._

“ So what kind of stuff do you like?” Dean asked breaking Castiel from his concerns and doubts. “Your friends said you were...how did they put it? A nerd?” Dean chuckled, while Castiel turned bright red. 

“Well I like to game.  I mean I guess you could say I’m into some pretty nerdy shows and movies.” Castiel said. All the things he knew and liked by heart just seemed to escape his cranium. 

“Movies? So like superheroes?” Dean asked excitedly.

Castiel nodded. “Yeah. I’m very partial to Marvel.”

Dean made a look of disgust but laughed right after. “Marvel is good and I like the avengers but I’m more of a DC fan. Love batman.” 

Castiel couldn’t help but roll his eyes. “Of course, I totally pegged you as that.”

Dean gave him a shocked look. “Well then who is your favorite?”

“Captain America.” Castiel said without hesitation. He didn’t even have to think on that. He really liked Captain America, from his back story to his morals there was just something Castiel really enjoyed. It didn’t help he was very attractive to.

“He’s pretty awesome. I like Iron Man too.”

Castiel laughed and shook his head. “What is it about asshole millionaires with cool gadgets that you like?”

“Oh you know, they fact they are hot.” Dean said.

Castiel choked on his drink and wrinkled his nose. “Really?” He didn’t really think that either one was very attractive.

Dean shook his head. “No not really. I’m straight actually, so...” Dean trailed off.

Castiel frowned and felt his stomach drop. Of course Dean was. Castiel never was that lucky. He took a deep breath and looked at Dean who had a concerned look on his face once again.

“Did I say  something wrong?” Dean asked.

Castiel forced a smile on his face and tried to let out a laugh that didn’t sound maniacal. “No why do you ask?”

“Your body language changed all of the sudden.” Dean said. “Your entire body just slumped down.”

 _Oh..._ Castiel always hated when people could read his body especially when he couldn’t read theirs.

“I’m fine.” Castiel said, waving his hand. He wasn’t sure if his attempt at playing it off worked or not as Dean just nodded and changed the subject.

“What do you do for a living?” Dean asked.

“I wok at a shop in the mall.” Castiel said. “Not super interesting but it pays the bills. What about you?”

“I work at a mechanics. I like it, I enjoy fixing up cars. My own car is a family car I fixed up.” Dean’s eyes lit up as he talked about his car. He had a real passion about it, Castiel could tell.

“What kind of car?”

“Oh, Baby is a 1967 Chevrolet Impala. She is beautiful. Four door, bench seats. She even has the original cassette player that my dad used when I was a kid.”

“Baby?” Castiel raised an eyebrow.

“Yeah, that’s her name.”

Dean looked so cute as he excitedly talked about his car. Castiel wanted to kick himself, he didn’t need to be let down once again. And he didn’t need to grow attached to yet another guy that would never be interested in him. He couldn’t deny that Dean was attractive, charismatic and overall very interesting. He seemed kind and good natured, down to earth.

“Where are you from?” Castiel asked.

“Oh...is it obvious?” Dean ducked his head in embarrassment. “I’m originally from Kansas. I’ve only lived here for a few months. I moved here actually because my brother goes to college here and he needed a roommate after he got kicked out of his dorm.”

“How...did he get kicked out?” Castiel asked, although he wasn’t sure if he really wanted to know.

“I don’t know the full story but it involved a friend of his and a badger. And no I have no idea where they got the badger.” Dean laughed.

“Well sounds like you have a pretty interesting life there. Or at least your brother does.” Castiel shook his head.

“Yeah, I guess.” Dean shrugged. “So what do you like to do on your days off then? It sounds like you hate your job, so what do you like?”

“Well I sort of just sit around at home playing video games. I don’t really go anywhere.”

Dean frowned. “Do you not like the outdoors?”

“Oh no I love it, I just don’t have anyone to do anything most of the time and I’m always at work it seems. I love to go hiking, but there isn’t many places within bus distance.”

“Well if you ever want a hiking buddy let me know.” Dean suggested.

Castiel was taken aback. This guy actually wanted to hang out with him? Sure Castiel was friendly, so he had been told, he always made friends easily. And this guy was no different than many of Castiel’s friends but they barely knew each other, plus they met at a random bar. He didn’t know if this guy was really a serial killer.

“I think we should exchange numbers first.” Castiel blurted out. _God dammit Cas, what the fuck are you doing?_ He scolded himself.

Dean shrugged and pulled out his phone. “Sure. Just put it in.” He said holding the phone out for Castiel.

As soon as Castiel had put his contact info into Dean’s phone, one of Dean’s friends seemed to decide that then was a great time to vomit onto the floor. Dean yelled out, taking his phone back and running over to his friend. Charlie shrieked and ran back over to where Castiel was.

“Fucking hell man!” Dean yelled at his buddy. “Look I gotta take him back home. It was nice meeting all of you.”

Castiel tried to say something but Charlie was already pulling him away from the scene, her hand over her mouth. Castiel threw one more glance to Dean who was helping his friend up before running after Charlie.

**Notes for the Chapter:**

> Follow me at actualcas.tumblr.com


End file.
